Dimethylamine → 4-Bromo-N,N-dimethylbenzylamine

A solution of 1-bromo-4-(bromomethyl)benzene (20 g, 80.65 mmol, 1.00 equiv), dimethylamine (13.20 g, 96.80 mmol, 1.20 equiv, 33%) and potassium carbonate (13.36 g, 96.81 mmol, 1.20 equiv) in ethanol (200 mL) was stirred overnight at 50° C. The solid material was removed by filtration and the filtrate was concentrated under vacuum. The residue was dissolved in 200 mL of water and extracted with 3×200 mL of dichloromethane. The combined organic layer was washed with 3×200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (20:1) to give 10 g (58%) of (4-bromophenyl)-N,N-dimethylmethanamine as a yellow oil. LC-MS: (ES, m/z): 255 [M+CH3CN+H]+, 214 [M+H]+, 169.

1. customThe solid material was removed by filtration
2. concentrationthe filtrate was concentrated under vacuum
3. dissolutionThe residue was dissolved in 200 mL of water
4. extractionextracted with 3×200 mL of dichloromethane
5. washThe combined organic layer was washed with 3×200 mL of brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. customThe residue was purified on a silica gel column
9. washeluted with dichloromethane/methanol (20:1)

ORD-Eintrag

ord-6525c9ab545a49f2a385c1c71864515b

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09296732B2